Vintage Celebrities Wearing Hats

These icons are proof that few things can glam up a look quite like a hat can

By
Hilary Shepherd

Jan 2, 2019

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Berets, caps, fedoras, pillbox hats, bowlers—the list goes on. From Josephine Baker’s famous top hat (the legendary entertainer and activist proudly paired it with a men’s tuxedo) and Jackie O’s classic pillbox hats to Mae West’s quintessential picture hat (replete with feathers and a slinky black gown) and Humphrey Bogart's archetypal fedora, these vintage icons are proof that nothing can zhuzh up a look more than a hat can. Click through the slideshow to see some of the chicest headgear throughout history.

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Jane Seymour

The English actress posing in a fur topper in London after signing on to star alongside Roger Moore in the British spy film Live and Let Die in 1972

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Josephine Baker

The iconic jazz entertainer and civil rights activist was one of the first women to break from the confines of sartorial gender roles, famously sporting a tuxedo and a top hat during her production of "La Joie de Paris" in 1932.

The film icon lounging on a boat in Switzerland in the early '50s donning a crochet hat with a pointed tip

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Joanna Lumley

The English Ab Fab star wearing a traditional men's bowler hat to emulate Patrick Macnee's character in the 1976 television series The New Avengers, which she starred in alongside him

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Humphrey Bogart

To play Rick Blaine in the 1942 film Casablanca, the silver screen legend wore a fedora and a trench coat. This became one of Bogart's most famous looks of all time.

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Frank Sinatra

The influential crooner donning his trademark straw fedora, the topper of choice for the members of the notorious 1960s "Rat Pack" group, which consisted of Sinatra, Humphrey Bogart, Dean Martin, and more

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Marlon Brando

The seminal screen star wearing a bolero hat in the 1961 adventure film One-Eyed Jacks, which he also directed.

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Zsa Zsa Gabor

The Hungarian actress and socialite in a wide-brimmed straw hat circa 1950

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Tony Curtis

Curtis in a traditional Ukrainian astrakhan hat on the set of the J. Lee Thompson-directed film Taras Bulba.

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Bianca Jagger

The actress and human rights advocate in a veiled cocktail hat adorned with feathers in 1972

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Liza Minnelli

The legendary performer in a sequined cap for a scene in Cabaret, the 1972 musical that earned her an Academy Award and a Golden Globe

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Barbara Streisand

The actress in a wide brim hat with ribbon detailing as Fanny Brice in Funny Girl

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Brigitte Bardot

The French icon sporting her signature beret—the quintessential symbol of Parisian chic throughout the '60s and '70s

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Angela Lansbury

A tall, brim-less cap in leopard print was part of Lansbury's character as Elfie van Donck in the 1965 television series The Man from U.N.C.L.E.

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Grace Kelly

The Princess of Monaco in a fez-style hat at the opening of the Monaco Karting Club in 1962

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Robert Redford

The screen legend sporting a traditional police officer cap in the Peter Yates-directed action film The Hot Rock

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Queen Elizabeth II

The Queen in a coral-colored halo-style hat during a visit to the Isle of Wright in 1965

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Sophia Loren

The Italian actress wearing a swimming cap-style topper with a leather chin strap at the airport in London in 1965

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Mae West

The bawdy actress lying on chaise in her quintessential uniform of a slinky black gown and a large feathered picture hat

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Judy Garland

The Golden Era icon tipping her trilby hat to the side circa 1950

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Joan Crawford

The outspoken film star touching down in London in a flat, wide-brimmed hat

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Princess Diana

The Princess of Wales in a veiled black bowler hat designed by Viv Knowland during a visit to Paris in 1988

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Faye Dunaway

The actress wearing a peach-colored halo hat playing Vicki Anderson in the 1986 film The Thomas Crown Affair

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Jackie Kennedy Onassis

The first lady wearing her signature pillbox hat during the launch of the USS Lafayette submarine in 1962

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